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. 2014 Aug 18;53(34):9012-6.
doi: 10.1002/anie.201404191. Epub 2014 Jun 24.

Bioinspired total synthesis of sespenine

Yu Sun  1 , Pengxi Chen, Deliang Zhang, Martin Baunach, Christian Hertweck, Ang Li
Affiliations

Bioinspired total synthesis of sespenine

Yu Sun et al. Angew Chem Int Ed Engl. .

Abstract

The first total synthesis of sespenine, a rare indole sesquiterpenoid from a mangrove endophyte, has been accomplished. A bioinspired aza-Prins/Friedel-Crafts/retro Friedel-Crafts cascade reaction assembles the bridged tetrahydroquinoline core. Further investigations on the aza-Prins cyclization imply that the C3 configuration of the hydroxyindolenine intermediate is crucial to the biosynthesis of sespenine and its congener xiamycin A.

Keywords: biomimetic synthesis; cyclization; heterocycles; natural products; total synthesis.

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